(E/Z)-2,2-dimethyl-4-undecen-3-one | 727381-77-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E/Z)-2,2-dimethyl-4-undecen-3-one
• 英文别名: 2,2-Dimethylundec-4-en-3-one；2,2-dimethylundec-4-en-3-one
• CAS: 727381-77-3
• 化学式: C₁₃H₂₄O
• 分子量: 196.333
• InChiKey: VISOPJSYPCILSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E/Z)-2,2-dimethyl-4-undecen-3-one 在 二氯[(S)-(-)-2,2'-双(二对甲苯基膦基)-1,1'-联萘](2-氨甲基吡啶)钌(II)RUCL2(AMPY) 、 potassium tert-butylate 、 氢气 作用下， 以 乙醇 为溶剂， 27.0 ℃ 、810.6 kPa 条件下， 反应 5.0h， 生成 (E)-(S)-2,2-Dimethyl-undec-4-en-3-ol 、 (R)-(E)-2,2-dimethyl-4-undecen-3-ol
  参考文献：
  名称：

  Asymmetric Hydrogenation of tert-Alkyl Ketones

  摘要：

  A combined system of RuCl2(tolbinap)(pica) and an alkaline or organic phosphazene base catalyzes asymmetric hydrogenation of sterically congested tert-alkyl ketones (TolBINAP = 2,2'-bis(di-4-tolylphosphino)-1,1'-binaphthyl, PICA = alpha-picolylamine). Hydrogenation with RuH(eta1-BH4)(tolbinap)(pica) does not require any strong base. Alcoholic solvents strongly affect the catalytic efficiency. The reaction proceeds smoothly in ethanol under 1-20 atm of H2 and at room temperature with a substrate to catalyst molar ratio of up to 100 000. Various aliphatic, aromatic, heteroaromatic, and olefinic tert-alkyl ketones are convertible to the corresponding chiral carbinols in high enantiomeric purity. Olefinic and heteroaromatic functions are left intact. Certain cyclic ketones are also usable. The mode of enantioface selection is consistent and predictable.

  DOI：

  10.1021/ja052071+

文献信息

• Ruthenium Complex and Process for Producing Tert-Alkyl Alcohol Therewith
  申请人：Ohkuma Takeshi

  公开号：US20070265448A1

  公开（公告）日：2007-11-15

  A tert-alkyl ketone, pinacolone was hydrogenated under pressurized hydrogen in the presence of a ruthenium complex (S)-1 and a base, and corresponding (S)-3,3,-dimethyl-2-butanol was thereby obtained in 100% yield and 97% ee.

  在氢气的压力下，在钌络合物（S）-1和碱的存在下，对一种三级烷基酮，皮那酮进行了加氢反应，从而获得了相应的（S）-3,3-二甲基-2-丁醇，收率为100％，旋光度为97％ ee。
• RUTHENIUM COMPLEX AND PROCESS FOR PRODUCING TERT-ALKYL ALCOHOL THEREWITH
  申请人：Nagoya Industrial Science Research Institute

  公开号：EP1813621A1

  公开（公告）日：2007-08-01

  A tert-alkyl ketone, pinacolone was hydrogenated under pressurized hydrogen in the presence of a ruthenium complex (S)-1 and a base, and corresponding (S)-3,3,-dimethyl-2-butanol was thereby obtained in 100% yield and 97% ee.

  在钌络合物 (S)-1 和碱的存在下，在加压氢气的作用下对叔烷基酮频哪酮进行氢化，从而得到相应的 (S)-3,3,-二甲基-2-丁醇，收率为 100%，ee 为 97%。
• [DE] KONDENSATIONSPRODUKT<br/>[EN] CONDENSATION PRODUCTS<br/>[FR] PRODUITS DE CONDENSATION
  申请人：HENKEL KOMMANDITGESELLSCHAFT AUF AKTIEN

  公开号：WO1996025382A1

  公开（公告）日：1996-08-22

  (DE) Die Erfindung betrifft ein Kondensationsprodukt aus Isononylaldehyd und Methylethylketon. Es enthält die Isomeren 3,6,8,8-Tetramethylnon-3-en-2-on und 7,9,9-Trimethyl-4-decen-3-on zu mindestens 85 Gew.-%, wobei diese Isomeren im Gewichtsverhältnis von 1:10 bis 10:1 vorliegen. Das Geruchsprofil zeichnet sich durch eine Citrus-/Bergamotte-Charakteristik aus.(EN) The invention relates to a condensation product of isononyl aldehyde and methylethyl ketone. It contains the isomers 3,6,8,8-tetramethylnon-3-en-2-one and 7,9,9-trimethyl-4-decen-3-one in a proportion of at least 85 wt.%, in which said isomers are in the ratio by weight of 1:10 to 10:1. This product is characterized by a citrus-bergamot aroma.(FR) L'invention concerne un produit de condensation d'isononylaldéhyde et de méthyléthylcétone. Ce produit contient les isomères 3,6,8,8-tétraméthylnon-3-èn-2-one et 7,9,9-triméthyl-4-décèn-3-one dans une proportion d'au moins 85 % en poids, le rapport de poids de ces isomères étant compris entre 1:10 et 10:1. Ce produit se caractérise par un arôme citrus-bergamote.

  该发明涉及isononyl aldehyde和methylethyl ketone的蒸馏产物。该产物含有三种异构体，其中含有3,6,8,8-tetramethylnon-3-en-2-one和7,9,9-trimethyl-4-dec-3-one，重量百分比至少为85%。其中，这两种异构体的重量比在1:10到10:1之间。该产物具有柑橘香和 bergamot 味觉得出。
• US7378560B2
  申请人：——

  公开号：US7378560B2

  公开（公告）日：2008-05-27
• Asymmetric Hydrogenation of <i>tert</i>-Alkyl Ketones
  作者：Takeshi Ohkuma、Christian A. Sandoval、Rajagopal Srinivasan、Quinghong Lin、Yinmao Wei、Kilian Muñiz、Ryoji Noyori

  DOI：10.1021/ja052071+

  日期：2005.6.1

  A combined system of RuCl2(tolbinap)(pica) and an alkaline or organic phosphazene base catalyzes asymmetric hydrogenation of sterically congested tert-alkyl ketones (TolBINAP = 2,2'-bis(di-4-tolylphosphino)-1,1'-binaphthyl, PICA = alpha-picolylamine). Hydrogenation with RuH(eta1-BH4)(tolbinap)(pica) does not require any strong base. Alcoholic solvents strongly affect the catalytic efficiency. The reaction proceeds smoothly in ethanol under 1-20 atm of H2 and at room temperature with a substrate to catalyst molar ratio of up to 100 000. Various aliphatic, aromatic, heteroaromatic, and olefinic tert-alkyl ketones are convertible to the corresponding chiral carbinols in high enantiomeric purity. Olefinic and heteroaromatic functions are left intact. Certain cyclic ketones are also usable. The mode of enantioface selection is consistent and predictable.